A tetradentate ring metal platinum complex phosphorescent material and its application

Abstract

The present invention provides a tetradentate metal platinum complex phosphorescent material based on pyridine heterocycle, benzoxazole and carbazole derivatives. It is a novel 6 / 6 / 6 metal-cyclophenol oxygen coordinated tetradentate platinum (II) complex phosphorescent material. The N-C-N-N tetradentate cyclopentane structure system phosphorescent material of the present invention has the characteristics of easy adjustment of HOMO and LUMO orbital energy levels and strong luminescence; and has good chemical stability and thermal stability, and is easy to prepare vapor deposition type OLED devices.

Description

Technical Field

[0001] The invention relates to a phosphorescent material and application thereof, in particular to a tetradentate ring metal platinum complex phosphorescent material and application thereof. Background Art

[0002] Organic Light-Emitting Diode (OLED) refers to a device structure in which, under the action of an external electric field, electrons and holes enter the light-emitting layer to recombine to form excitons in a sandwich structure, and then transition to the ground state to emit radiation. Compared with traditional electrodeless light-emitting diodes (Liquid Crystal Display, LCD), OLED has the advantages of low energy consumption, good performance, high brightness, self-luminescence and wide visibility, and is very popular and widely used in the field of display lighting.

[0003] In electroluminescence, 25% of singlet excitons and 75% of triplet excitons are formed according to spin statistics. In the initial OLED devices, fluorescent materials were mainly used. In theory, only 25% of singlet excitons can be used, and the remaining 75% of triplet excitons are lost in the form of non-radiative transitions, which seriously limits the development of OLEDs and has extremely low external quantum efficiency. Phosphorescent materials introduce heavy metal atoms to induce the self-selected orbital coupling effect, break the transition barrier, and enable triplet excitons to transition downward to the ground state, achieving 100% exciton utilization. Generally, cyclometallated platinum complex phosphorescent materials are formed by coordination of suitable ligand structures and metal platinum atoms. Modifying the chemical structure of the ligand can effectively change the luminescent properties of the metal complex. Compared with bidentate and tridentate ligand structures, the rigid structure of the tetradentate complex can inhibit vibration coupling, reduce non-radiative transitions, and improve the luminescence quantum efficiency, thereby achieving efficient phosphorescent emission. Although the development momentum of tetradentate metal platinum complexes is strong at present, efficient and stable platinum complexes have yet to be developed. Therefore, the development of new tetradentate metal platinum complexes is still a top priority in the OLED field. Summary of the invention

[0004] In order to develop more types of higher performance phosphorescent materials, the purpose of the present invention is to provide a tetradentate metal platinum complex phosphorescent material and its application. The present invention uses tetradentate ligands of pyridine heterocycles, benzoazoles and carbazole derivatives to develop a new 6 / 6 / 6 metal ring structure to obtain a new type of tetradentate metal platinum complex phosphorescent material. Using it as a light-emitting layer to prepare an organic electroluminescent device can make the device have excellent performance. It can improve the external quantum efficiency of the organic electroluminescent device and reduce the turn-on voltage.

[0005] To achieve the above technical objectives, the technical solution of the present invention is as follows:

[0006] The present invention provides a tetradentate metal platinum complex phosphorescent material having a general structure as shown in formula (I):

[0007]

[0008] Wherein, X is CR1R2 or NR3; X1 is selected from NR4, O or S; R1-R4 are each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 cycloalkyl, substituted or unsubstituted C1-C30 heterocycloalkyl, substituted or unsubstituted C1-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C6-C18 heterocyclicamine, and combinations thereof;

[0009] Y 1 -Y 16 are each independently selected from C or N;

[0010] R a , R b , R c , R d and R e Each independently represents a single substitution to the maximum amount of substitution, or no substitution; each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 cycloalkyl, substituted or unsubstituted C1-C30 heterocycloalkyl, substituted or unsubstituted C1-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl, and the group consisting of; said R1-R4, R a , R b , R c , R d and R e At least one hydrogen in the group may be replaced by deuterium, and the substituent in the “substituted or unsubstituted” group is selected from one or more of deuterium, halogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, and phenyl. In the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other; when containing heteroatoms, the heteroatoms are selected from O or N; the R1-R4, R a , R b , R c , R d and R e Two or more adjacent substituents may independently or selectively be linked to form a fused ring.

[0011] Preferably, the tetradentate metal platinum complex phosphorescent material has a general structure as shown in formula (I-1) or formula (I-2):

[0012]

[0013] Among them, Y 17 -Y 27 are each independently selected from C or N;

[0014] R f , R g and R h Each independently represents mono-substitution to the maximum amount of substitution, or no substitution; each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C30 alkyl, C1-C30 haloalkyl, substituted or unsubstituted C1-C30 cycloalkyl, substituted or unsubstituted C1-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl, and the group consisting of;

[0015] The substituent in the "substituted or unsubstituted" is selected from one or more of deuterium, trifluoromethyl, halogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, phenyl, biphenyl, and in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other; when containing heteroatoms, the heteroatoms are selected from O or N; the R f , R g and R h At least one hydrogen in may be replaced by deuterium, and two or more adjacent substituents may be independently or selectively linked to form a condensed ring.

[0016] Preferably, in formula (I), (I-1) and (I-2), R a , R b , R c , R d and R e Each is independently selected from hydrogen, deuterium, F, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, phenyl, furanyl, benzofuranyl, pyridyl, and the group consisting of.

[0017] Preferably, in formula (I-1) and (I-2), R f , R g and R h Each is independently selected from hydrogen, deuterium, F, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, phenyl, furanyl, benzofuranyl, pyridyl, and the group consisting of.

[0018] Preferably, R4 is selected from hydrogen, deuterium, F, methyl, ethyl, propyl, tert-butyl, phenyl, biphenyl, methylbenzene, tert-butylphenyl, benzofuranyl, pyridyl, and the group consisting thereof.

[0019] Preferably, the R g and R h Each is independently selected from the group consisting of hydrogen, methyl, tert-butyl, tert-butylbenzene, and the like.

[0020] Preferably, the tetradentate metal platinum complex phosphorescent material is selected from any one of the following structural formulas:

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038] Furthermore, the present invention also provides the use of the tetradentate metal platinum complex phosphorescent material having the structures shown in formula (I) to formula (V) in electronic devices.

[0039] Furthermore, the electronic devices include organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQDs), light emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

[0040] In another aspect, the present invention further provides an organic electroluminescent device, which comprises the tetradentate metal platinum complex phosphorescent material having a structure represented by formula (I), (I-1) or (I-2) as described above.

[0041] Furthermore, the organic electroluminescent device comprises a cathode, an anode and an organic functional layer therebetween; the organic functional layer comprises the tetradentate metal platinum complex phosphorescent material having a structure shown in formula (I), (I-1) or (I-2) as described above.

[0042] Preferably, the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises the tetradentate metal platinum complex phosphorescent material having the structure shown in formula (I), (I-1) or (I-2) as described above.

[0043] Furthermore, the light-emitting layer further comprises a host material, and the mass percentage of the tetradentate ring metal platinum complex phosphorescent material is 1% to 50%. The host material is not limited.

[0044] In another aspect, the present invention also provides an organic photoelectric device, which comprises: a substrate layer; a first electrode, the first electrode being on the substrate; an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode; a second electrode, the second electrode being on the organic light-emitting functional layer; wherein the organic light-emitting functional layer comprises a tetradentate metal platinum complex phosphorescent material having a structure as shown in formula (I), (I-1) or (I-2) above. For example, the tetradentate metal platinum complex can be included in the organic light-emitting functional layer as a light-emitting material.

[0045] Furthermore, the organic light-emitting functional layer further comprises a host material, and the mass percentage of the tetradentate ring metal platinum complex phosphorescent material is between 1% and 50%. The host material is not limited.

[0046] In the present invention, the organic photoelectric device can be prepared by evaporating metal or conductive oxides and their alloys on a substrate to form an anode by using a method such as sputtering coating, electron beam evaporation, vacuum evaporation, etc.; a hole injection layer, a hole transport layer, a light-emitting layer, an air blocking layer and an electron transport layer are sequentially evaporated on the surface of the prepared anode, and then a cathode is evaporated. In addition to the above method, an organic electroluminescent device is prepared by evaporating a cathode, an organic layer and an anode on a substrate in sequence. The organic layer can also include a multilayer structure such as a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer and an electron transport layer. In the present invention, the organic layer is prepared by using a polymer material according to solvent engineering (spin-coating, tape-casting, doctor-blading, screen-printing, inkjet printing or thermal-imaging, etc.) instead of the evaporation method, which can reduce the number of device layers.

[0047] The present invention also provides a composition, which comprises a tetradentate metal platinum complex phosphorescent material having a structure as shown in formula (I), (I-1) or (I-2). Preferably, the composition further comprises a fluorescent doping material, and the fluorescent doping material is preferably a boron-containing organic molecular luminescent material, preferably a phosphorescence-sensitized boron-containing compound.

[0048] The present invention also provides a preparation, which comprises a tetradentate metal platinum complex phosphorescent material having a structure shown in formula (I), (I-1) or (I-2) or a composition as described above and at least one solvent.

[0049] The solvent is not particularly limited and may be used, for example, unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, butyl chloride, butyl bromide, pentyl chloride, pentyl bromide, hexyl chloride, hexyl bromide, cyclohexyl chloride, cyclohexyl bromide, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran, tetrahydropyran, and ester solvents such as alkyl benzoate.

[0050] The present invention also provides a display or lighting device, which comprises one or more of the organic photoelectric devices described above.

[0051] Compared with the prior art, the present invention has the following beneficial effects:

[0052] The present invention provides a tetradentate metal platinum complex phosphorescent material based on pyridine heterocycle, benzoxazole and carbazole derivatives. It is a novel 6 / 6 / 6 metal-cyclophenol oxygen coordinated tetradentate platinum (II) complex. The NCNN tetradentate cyclopentane structure system phosphorescent material of the present invention has the characteristics of easy adjustment of HOMO and LUMO orbital energy levels and strong luminescence; and has good chemical stability and thermal stability, and is easy to prepare vapor deposition type OLED devices. The organic electroluminescent device made of the compound of the present invention as the light-emitting layer can reduce the light-on voltage and significantly improve the external quantum efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0053] Figure 1 It is the emission spectra of compounds Pt1, Pt2, Pt3 and Pt4 in a dichloromethane solution at room temperature under deoxygenated conditions;

[0054] Figure 2 This is a schematic diagram of the HOMO and LUMO orbital distribution of the compound Pt513-Pt516;

[0055] Figure 3 This is a schematic diagram of the HOMO and LUMO orbital distribution of the compound Pt517-Pt520. DETAILED DESCRIPTION

[0056] The contents of the present invention will be described in detail below. The description of the constituent elements described below may be based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples.

[0057] The term "substituted" used in the present invention is intended to include all allowed substituents of organic compounds. In a wide aspect, allowed substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and non-aromatic substituents of organic compounds. Illustrative substituents include, for example, those described below. For suitable organic compounds, allowed substituents can be one or more, the same or different. For the purpose of the present invention, the present invention is not intended to be any restriction in any way with the allowed substituents of organic compounds. Similarly, the term "substituted" or "substituted with" contains implicit conditions that this substitution conforms to the allowed valence of the substituted atom and the substituent, and the substitution leads to a stable compound (for example, a compound that will not spontaneously undergo transformation (for example, by rearrangement, cyclization, elimination, etc.)). It is also expected that, in some aspects, unless explicitly indicated to the contrary, a single substituent can be further optionally substituted (that is, further substituted or unsubstituted).

[0058] In defining various terms, R1-R4, R a , R b , R c, R d and R e In the present invention, the symbols are used as general symbols to represent various specific substituents. These symbols can be any substituent, not limited to those disclosed in the present invention, and when they are limited to certain substituents in one case, they can be limited to some other substituents in other cases. a , R b , R c , R d and R e Can independently have one or more of the groups listed above. For example, if R 1 If it is a straight chain alkyl, then one of the hydrogen atoms of the alkyl may be optionally substituted with a hydroxyl, alkoxy, alkyl, halogen, etc. Depending on the groups selected, the first group may be incorporated within the second group, or alternatively, the first group may be pendant, ie attached to the second group.

[0059] The term "alkyl" used in the present invention is a saturated hydrocarbon group of 1 to 60 carbon atoms that is branched or unbranched, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, etc. The alkyl group may be cyclic or acyclic. The alkyl group may be branched or unbranched. The alkyl group may also be substituted or unsubstituted. For example, the alkyl group may be substituted with one or more groups, including but not limited to the optionally substituted alkyl, cycloalkyl, alkoxy, amino, halogen, hydroxyl, nitro, silyl, sulphur-oxo or sulfhydryl groups of the present invention.

[0060] The term "aryl" used in the present invention is a group containing any carbon-based aromatic group of 5 to 60 carbon atoms, and the carbon-based aromatic group includes but is not limited to phenyl, naphthyl, phenyl, biphenyl, phenoxyphenyl, anthracenyl, phenanthrenyl, etc. The term "aryl" also includes "heteroaryl", which is defined as a group containing an aromatic group, and the aromatic group has at least one heteroatom introduced into the ring of the aromatic group. Examples of heteroatoms include but are not limited to nitrogen, oxygen, sulfur, and phosphorus. Similarly, the term "non-heteroaryl" (which is also included in the term "aryl") defines a group containing an aromatic group, and the aromatic group does not contain heteroatoms. Aryl can be substituted or unsubstituted. The aryl group may be substituted with one or more groups, including but not limited to the alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxyl, ester, halogen, hydroxyl, carbonyl, azido, nitro, silyl, sulfo-oxo or thiol groups described herein.

[0061] Compounds of the present invention may contain "optionally substituted" parts. Typically, the term "substituted" (whether or not the term "optionally" is present in the front) means that one or more hydrogens of the indicated part are replaced by suitable substituents. Unless otherwise specified, "optionally substituted" groups may have suitable substituents at each substitutable position of the group, and when more than one position may be substituted with more than one substituent selected from a specified group in any given structure, the substituents at each position may be the same or different. The substituent combinations envisioned by the present invention are preferably those that form stable or chemically feasible compounds. In some respects, unless clearly indicated to the contrary, it is also contemplated that each substituent may be further optionally substituted (that is, further substituted or unsubstituted).

[0062] The compounds disclosed herein can exhibit desirable properties and have emission and / or absorption spectra that can be tuned by selecting appropriate ligands. In another aspect, the invention can exclude any one or more compounds, structures or portions thereof specifically recited herein.

[0063] The compounds of the present invention may be prepared using a variety of methods, including but not limited to those described in the examples provided herein.

[0064] It should be noted that the above general description and the following detailed description are only exemplary and explanatory, and are not limiting. The present application can be more easily understood by referring to the following specific implementation manner and the examples contained therein.

[0065] Before disclosing and describing the compounds, devices and / or methods of the present invention, it should be understood that they are not limited to specific synthetic methods (otherwise otherwise indicated), or specific reagents (otherwise otherwise indicated), as this can of course vary. It should also be understood that the terms used in the present invention are only used for the purpose of describing specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described in the present invention can be used in the practice or test, exemplary methods and materials are described below. Synthesis Examples All raw materials and solvents are commercially available unless otherwise specified, and solvents are used directly without further treatment.

[0066] The substrate of the present invention can be any substrate used in typical organic optoelectronic devices. It can be a glass or transparent plastic substrate, or a substrate of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, the use direction is different. As the material for the hole injection layer, the hole transport layer, and the electron injection layer, any material can be selected from the known related materials for OLED devices, and the present invention does not make specific restrictions thereon.

[0067] Synthesis Example

[0068] The following examples of compound synthesis, composition, device or method are only to provide a general method for the industry, and are not intended to limit the scope of protection of the patent. The data (quantity, temperature, etc.) mentioned in the patent are as accurate as possible, but there may be some errors. Unless otherwise specified, weighing is separate weighing, temperature is ℃, or room temperature, and pressure is close to normal pressure.

[0069] The following examples provide methods for preparing new compounds, but the preparation of such compounds is not limited to this method. In this professional and technical field, since the protected compounds in the present invention are easy to modify and prepare, their preparation can adopt the following methods or other methods. The following examples are only examples and are not intended to limit the scope of protection of this patent. Temperature, catalyst, concentration, reactants and reaction process can all be changed to select different conditions for preparing the compounds for different reactants.

[0070] 1 H NMR (500MHz), 1 H NMR (400MHz), 13 C NMR (126 MHz) spectra were measured on an ANANCE III (500 M) NMR spectrometer. Unless otherwise specified, DMSO-d6 or CDCl3 containing 0.1% TMS was used as the solvent for NMR. 1 When CDCl3 is used as the solvent, TMS (δ=0.00 ppm) is used as the internal standard in the HNMR spectrum; when DMSO-d6 is used as the solvent, TMS (δ=0.00 ppm) or the residual DMSO peak (δ=2.50 ppm) or the residual water peak (δ=3.33 ppm) is used as the internal standard. 13 In the C NMR spectrum, CDCl3 (δ=77.00 ppm) or DMSO-d6 (δ=39.52 ppm) was used as the internal standard. HPLC-MS was measured on an Agilent 6210TOF LC / MS mass spectrometer; HRMS spectrum was measured on an Agilent 6210TOF LC / MS liquid chromatography-time of flight mass spectrometer. 1 In H NMR spectrum data: s = singlet, d = doublet, t = triplet, q = quartet, p = quintet, m = multiplet, br = broad.

[0071] Example 1: Synthesis of Tetradentate Ring Metal Platinum Complex Pt1:

[0072]

[0073] (1) Synthesis of ligand Ligand1: 1-Bpin (174 mg, 0.47 mmol, 1.0 equivalent), CZ-Br (300 mg, 0.49 mmol, 1.05 equivalent), tetrakistriphenylphosphine palladium (16 mg, 0.014 mol, 3 mol%) and potassium carbonate (195 mg, 1.41 mmol, 3.0 equivalent) were added to the reaction tube in sequence, nitrogen was replaced three times, 1,4-dioxane (5 mL) and water (1 mL) were added under nitrogen protection, and the mixture was placed in an oil bath at 85°C for reaction for 12 hours, cooled to room temperature, washed with water, extracted with ethyl acetate, the aqueous layer was extracted with ethyl acetate three times, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / ethyl acetate = 20:1-10:1, and 70 mg of white solid was obtained, with a yield of 19%. 1 H NMR (500MHz, CDCl3): δ (ppm) 1.10 (s, 10H), 1.38 (s, 9H), 1.40 (s, 9H), 7.14-7.19 (m, 3H), 7.34 (d, J =8.5Hz,1H),7.40-7.44(m,3H),7.50-7.54(m,4H),7.70(d,J=8.5Hz,3H),7.91(d,J=8.5Hz,1H),7 .97(d,J=8.0Hz,1H),8.14(dd,J=8.0,1.5Hz,1H),8.23(d,J=1.5Hz,1H),8.26(d,J=1.5Hz,1H),8. 36(d,J=7.5Hz,1H),8.39-8.42(m,1H),8.47(d,J=8.0Hz,1H),8.94(d,J=1.0Hz,1H),11.24(s,1H).

[0074] (2) Synthesis of Pt1: Ligand1 (70 mg, 0.091 mmol, 1.0 equivalent), potassium chloroplatinate (40 mg, 0.095 mmol, 1.05 equivalent), tetrabutylammonium bromide (3 mg, 0.009 mmol, 0.1 equivalent) were added to a 50 mL dry three-necked flask equipped with a magnetic rotor and a condenser. The nitrogen was replaced three times, and acetic acid (6 mL) was added. After nitrogen was bubbled through the reaction liquid for 30 minutes, the mixture was stirred at room temperature for 12 hours, and then reacted at 120°C for 48 hours. The mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / dichloromethane = 3:1-1:1, to obtain 52 mg of a yellow solid with a yield of 59%. 1H NMR (500MHz, CDCl3): δ (ppm) 1.11 (s, 9H), 1.41 (s, 9H), 1.48 (s, 9H), 6.66-6.73 (m, 2H), 7.05 (dd, J = 7.5, 0.5Hz, 1H),7.10(dd,J=9.0,2.0Hz,1H),7.42-7.49(m,2H),7.52(dd,J=8.5,2.0Hz,1H),7.54-7.59(m,1H),7.66(d,J=2 .0Hz,1H),7.69(dd,J=8.0,2.0Hz,1H),7.73(dd,J=8.5,2.0Hz,1H),7.81(dd,J=8.0,2.0Hz,1H),7.84(ddd,J=8. 5,7.0,1.5Hz,1H),7.97(d,J=8.0Hz,1H),8.09-8.21(m,6H),8.28(d,J=2.0Hz,1H),9.22(dd,J=6.0,1.5Hz,1H).

[0075] Example 2: Synthesis of Tetradentate Ring Metal Platinum Complex Pt2:

[0076]

[0077] (1) Synthesis of ligand Ligand2: 2-Bpin (247 mg, 0.60 mmol, 1.0 equivalent), CZ-Br (400 mg, 0.66 mmol, 1.1 equivalent), tetrakistriphenylphosphine palladium (21 mg, 0.018 mol, 3 mol%) and potassium carbonate (249 mg, 1.80 mmol, 3.0 equivalent) were added to the reaction tube in sequence, and nitrogen was replaced three times. 1,4-dioxane (5 mL) and water (1 mL) were added under nitrogen protection, and the mixture was placed in an oil bath at 85°C for reaction for 12 hours, cooled to room temperature, washed with water, extracted with ethyl acetate, and the aqueous layer was extracted with ethyl acetate three times, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / ethyl acetate = 20:1-10:1, and 141 mg of white solid was obtained, with a yield of 23%. .

[0078] (2) Synthesis of Pt2: Ligand2 (120 mg, 0.15 mmol, 1.0 equivalent), potassium chloroplatinate (64 mg, 0.16 mmol, 1.05 equivalent), tetrabutylammonium bromide (5 mg, 0.015 mmol, 0.1 equivalent) were added to a 50 mL dry three-necked flask equipped with a magnetic rotor and a condenser. The nitrogen was replaced three times, and acetic acid (9 mL) was added. After nitrogen was bubbled through the reaction liquid for 30 minutes, the mixture was stirred at room temperature for 12 hours, and then reacted at 120°C for 48 hours. The mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / dichloromethane = 3:1-1:1, to obtain 50 mg of a yellow solid product with a yield of 34%. 1 H NMR (400MHz, DMSO-d6): δ (ppm) 1.06 (s, 9H), 1.34 (s, 3H), 1.39 (s, 9H), 1.43 (s, 9H), 1 .97(s,3H),6.00(d,J=8.8Hz,1H),6.98-7.11(m,3H),7.33(t,J=7.2Hz,2H),7.39-7. 57(m,6H),7.68(d,J=8.0Hz,1H),7.74(d,J=8.4Hz,1H),7.92(d,J=8.8Hz,1H),7.96- 8.08(m,3H),8.10(d,J=7.6Hz,1H),8.18(s,1H),8.37(s,1H),8.83(d,J=6.0Hz,1H).

[0079] Example 3: Synthesis of Tetradentate Metal Platinum Complex Pt3:

[0080]

[0081] (1) Synthesis of Ligand 3: 3-Bpin (148 mg, 0.40 mmol, 1.0 equivalent), CZ-Br (255 mg, 0.42 mmol, 1.05 equivalent), tetrakistriphenylphosphine palladium (14 mg, 0.012 mol, 3 mol%) and potassium carbonate (166 mg, 1.20 mmol, 3.0 equivalent) were added to the reaction tube in sequence, and nitrogen was replaced three times. 1,4-dioxane (4 mL) and water (1 mL) were added under nitrogen protection, and the mixture was placed in an oil bath at 85°C for reaction for 12 hours, cooled to room temperature, washed with water, extracted with ethyl acetate, the aqueous layer was extracted with ethyl acetate three times, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / ethyl acetate = 20:1-10:1, and 292 mg of white solid was obtained, with a yield of 95%. 1H NMR (400MHz, DMSO-d6): δ (ppm) 1.06 (s, 9H), 1.35 (s, 9H), 1.38 (s, 9H), 6.70 (d, J = 8.4Hz, 1H), 7.08 (d, J = 1.6Hz, 1H),7.14-7.27(m,4H),7.36(dd,J=7.6,4.8Hz,1H),7.44(t,J=7.2Hz,1H),7.48-7.49(m,2H),7.64-7.69(m,2H) ,7.71(d,J=7.2Hz,1H),7.80-7.82(m,2H),7.89(t,J=7.6Hz,1H),8.16(d,J=1.6Hz,1H),8.20(d,J=1.6Hz,1H),8 .26-8.29(m,2H),8.43(dd,J=4.8,1.6Hz,1H),8.61(t,J=1.6Hz,1H),8.66(dd,J=7.6,1.6Hz,1H),11.00(s,1H).

[0082] (2) Synthesis of Pt3: Pt3 (233 mg, 0.30 mmol, 1.0 equivalent), potassium chloroplatinate (132 mg, 0.32 mmol, 1.05 equivalent), tetra-n-butylammonium bromide (10 mg, 0.03 mmol, 0.1 equivalent) were added to a 50 mL dry three-necked flask equipped with a magnetic rotor and a condenser. The nitrogen was replaced three times, and acetic acid (18 mL) was added. After nitrogen was bubbled through the reaction liquid for 30 minutes, the mixture was stirred at room temperature for 12 hours, and then reacted at 120°C for 48 hours. The mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / dichloromethane = 3:1-1:1, to obtain 140 mg of a yellow solid product with a yield of 48%. 1H NMR (400MHz, DMSO-d6): δ (ppm) 1.06 (s, 9H), 1.27 (s, 9H), 1.44 (s, 9H), 4.69 (d, J = 8.8Hz, 1H), 6.63 (dd, J = 8.8, 2.0Hz,1H),7.05(d,J=8.0Hz,1H),7.31(dd,J=7.6,6.0Hz,1H),7.38(t,J=8.0Hz,1H),7.53(t,J=8.0Hz,1H),7 .56(d,J=1.6Hz,1H),7.63(t,J=7.6Hz,1H),7.72-7.90(m,5H),7.92(d,J=8.0Hz,1H),8.06(d,J=2.0Hz,1H),8 .16-8.25(m,2H),8.33(d,J=1.6Hz,1H),8.35(d,J=8.4Hz,1H),8.55-8.65(m,2H),9.01(dd,J=7.6,1.2Hz,1H).

[0083] Example 4: Synthesis of Tetradentate Ring Metal Platinum Complex Pt4:

[0084]

[0085] (1) Synthesis of Ligand 4: 4-Bpin (181 mg, 0.41 mmol, 1.0 equivalent), CZ-Br (300 mg, 0.41 mmol, 1.0 equivalent), tetrakistriphenylphosphine palladium (14 mg, 0.012 mol, 3 mol%) and potassium carbonate (169 mg, 1.22 mmol, 3.0 equivalent) were added to the reaction tube in sequence, and the nitrogen was replaced three times. 1,4-dioxane (4 mL) and water (1 mL) were added under nitrogen protection, and the mixture was placed in an oil bath at 85°C for reaction for 12 hours, cooled to room temperature, washed with water, extracted with ethyl acetate, the aqueous layer was extracted with ethyl acetate three times, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / ethyl acetate = 20:1-10:1, and 318 mg of white solid was obtained, with a yield of 92%. 1H NMR (400MHz, CDCl3): δ (ppm) 1.10 (s, 9H), 1.41 (s, 9H), 1.45 (s, 9H), 7.08-7.13 (m, 3H), 7.14 (d,J=1.6Hz,1H),7.15-7.20(m,3H),7.21-7.25(m,2H),7.33(td,J=7.6,0.8Hz,2H),7.35-7. 39(m,2H),7.42-7.51(m,4H),7.59-7.64(m,2H),7.66(t,J=1.6Hz,1H),7.75(t,J=7.2Hz,4H) ,8.05(d,J=1.6Hz,1H),8.08(s,1H),8.25(d,J=7.6Hz,1H),8.63-8.68(m,1H),11.03(s,1H).

[0086] (2) Synthesis of Pt4: Pt3 (231 mg, 0.27 mmol, 1.0 equivalent), potassium chloroplatinate (119 mg, 0.29 mmol, 1.05 equivalent), tetrabutylammonium bromide (9 mg, 0.027 mmol, 0.1 equivalent) were added to a 50 mL dry three-necked flask equipped with a magnetic rotor and a condenser. The nitrogen was replaced three times, and acetic acid (17 mL) was added. After nitrogen was bubbled through the reaction liquid for 30 minutes, the mixture was stirred at room temperature for 12 hours, and then reacted at 120°C for 48 hours. The mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / dichloromethane = 3:1-1:1, to obtain 200 mg of a yellow solid product with a yield of 71%. 1 H NMR (400MHz, CDCl3): δ (ppm) 1.09 (s, 9H), 1.22 (s, 9H), 1.45 (s, 9H), 4.84 (d, J = 8.8Hz, 1H), 6.39 (dd, J = 8.8, 2.0Hz, 1H),6.51-6.62(m,2H),6.91(t,J=7.6Hz,1H),7.04(d,J=8.0Hz,1H),7.09(d,J=8.4Hz,1H),7.17-7.22(m,2H),7.35 (d,J=7.6Hz,1H),7.45-7.52(m,2H),7.55(d,J=1.6Hz,1H),7.59(t,J=7.6Hz,1H),7.66-7.79(m,2H),7.86-8.04(m, 6H), 8.07 (d, J = 2.0Hz, 1H), 8.19 (d, J = 7.6Hz, 1H), 8.36 (d, J = 1.6Hz, 1H), 9.23-9.36 (m, 1H), 10.42 (d, J = 8.0Hz, 1H).

[0087] Example 5: Synthesis of Pt16

[0088] Pt16 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid of 562 mg with a yield of 60%. Molecular weight [M+H] + :885.2.

[0089] Example 6: Synthesis of Pt21

[0090] Pt-21 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (624 mg) with a yield of 59%. Molecular weight [M+H] + :885.2.

[0091] Example 7: Synthesis of Pt62

[0092] Pt-62 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (661 mg) with a yield of 72%. Molecular weight [M+H] + :939.2.

[0093] Example 8: Synthesis of Pt74

[0094] Pt-74 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (484 mg) with a yield of 61%. Molecular weight [M+H] + :885.2.

[0095] Example 9: Synthesis of Pt103

[0096] Pt-103 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (455 mg) with a yield of 65%. Molecular weight [M+H] + :928.3.

[0097] Example 10: Synthesis of Pt118

[0098] Pt118 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (410 mg) with a yield of 60%. Molecular weight [M+H] + :1003.3.

[0099] Example 11: Synthesis of Pt128

[0100] Pt128 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (492 mg) with a yield of 62%. Molecular weight [M+H] + :989.2.

[0101] Example 12: Synthesis of Pt140

[0102] Pt140 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (467 mg) with a yield of 61%. Molecular weight [M+H] + :1017.3.

[0103] Example 13: Synthesis of Pt157

[0104] Pt157 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (528 mg) with a yield of 68%. Molecular weight [M+H] + :1011.3.

[0105] Example 14: Synthesis of Pt171

[0106] Pt171 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (436 mg) with a yield of 48%. Molecular weight [M+H] + :812.2.

[0107] Example 15: Synthesis of Pt190

[0108] Pt190 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (410 mg) with a yield of 66%. Molecular weight [M+H] + :975.2.

[0109] Example 16: Synthesis of Pt224

[0110] Pt224 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (492 mg) with a yield of 82%. Molecular weight [M+H] + :1059.3.

[0111] Example 17: Synthesis of Pt263

[0112] Pt263 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (467 mg) with a yield of 72%. Molecular weight [M+H] + :885.2.

[0113] Example 18: Synthesis of Pt276

[0114] Pt276 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid of 528 mg with a yield of 68%. Molecular weight [M+H] + :1011.4.

[0115] Example 19: Synthesis of Pt319

[0116] Pt319 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (436 mg) with a yield of 49%. Molecular weight [M+H] + :1073.4.

[0117] Example 20: Synthesis of Pt345

[0118] Pt345 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (410 mg) with a yield of 66%. Molecular weight [M+H] + :1046.4.

[0119] Example 21: Synthesis of Pt395

[0120] Pt395 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (492 mg) with a yield of 82%. Molecular weight [M+H] + :1091.4.

[0121] Example 22: Synthesis of Pt410

[0122] Pt410 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (467 mg) with a yield of 72%. Molecular weight [M+H] + :1283.5.

[0123] Example 23: Synthesis of Pt442

[0124] Pt442 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (528 mg) with a yield of 63%. Molecular weight [M+H] + :927.2.

[0125] Example 24: Synthesis of Pt486

[0126] Pt486 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (436 mg) with a yield of 54%. Molecular weight [M+H] + :1016.3.

[0127] Example 25: Synthesis of Pt508

[0128] Pt508 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (410 mg) with a yield of 60%. Molecular weight [M+H] + :1140.3.

[0129] Example 26: Synthesis of Pt513

[0130] Pt513 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (492 mg) with a yield of 59%. Molecular weight [M+H] + :1095.5.

[0131] Example 27: Synthesis of Pt514

[0132] Pt514 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (467 mg) with a yield of 62%. Molecular weight [M+H] + :1122.5.

[0133] Example 28: Synthesis of Pt515

[0134] Pt515 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (528 mg) with a yield of 58%. Molecular weight [M+H] + :777.2.

[0135] Example 29: Synthesis of Pt516

[0136] Pt516 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (436 mg) with a yield of 52%. Molecular weight [M+H] + :778.2.

[0137] Example 30: Synthesis of Pt517

[0138] Pt517 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (410 mg) with a yield of 56%. Molecular weight [M+H] + :997.4.

[0139] Example 31: Synthesis of Pt518

[0140] Pt518 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (492 mg) with a yield of 62%. Molecular weight [M+H] + :1093.4.

[0141] Example 32: Synthesis of Pt519

[0142] Pt519 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (467 mg) with a yield of 66%. Molecular weight [M+H] +:817.3.

[0143] Example 33: Synthesis of Pt520

[0144] Pt520 was synthesized by referring to the synthesis steps and reaction conditions of compound Pt1. The target product was obtained as a yellow solid (528 mg) with a yield of 63%. Molecular weight [M+H] + :748.2.

[0145] Photophysical test and theoretical calculation description:

[0146] Steady-state emission experiments and lifetime measurements were performed on a Horiba Jobin Yvon FluoroLog-3 spectrometer. The Pt(II) complex was theoretically calculated using the Titan software package, and the geometry of the ground state (S0) molecule was optimized using density functional theory (DFT). The B3LYP functional was used for DFT calculations, with the 6-31G(d) basis set for C, H, O, S, and N atoms and the LANL2DZ basis set for Pt atoms.

[0147] Experimental data and analysis:

[0148] Figure 1 is the emission spectrum of compounds Pt1, Pt2, Pt3 and Pt4 in a dichloromethane solution at room temperature under deoxygenated conditions; Figure 1 It can be seen that some compounds Pt1, Pt2, Pt3 and Pt4 of the present invention can emit strong orange-red light and can be applied to OLED light-emitting layer materials.

[0149] Density functional theory (DFT) was used to calculate the compounds Pt513-Pt520. Table 1 is the DFT theoretical calculation data table. Figure 2 This is a schematic diagram of the HOMO and LUMO orbital distribution of the compound Pt513-Pt516; Figure 3 This is a schematic diagram of the HOMO and LUMO orbital distribution of the compound Pt517-Pt520.

[0150] Table 1. DFT theoretical calculation data

[0151]

[0152] From Table 1, Figure 2 , Figure 3It can be seen that Pt513, Pt514, Pt515, Pt516, etc. have similar HOMO orbital distributions, and the HOMO orbital distribution is concentrated on the carbazole group and the metal center Pt atom. Alkyl substitution and aryl substitution will significantly affect the size of their HOMO energy levels. The tert-butyl group can effectively improve its electron donation ability, so that the HOMO energy level of Pt513 increases from -4.90ev to -4.41ev compared with Pt515. The LUMO orbital distributions of Pt517, Pt518, Pt519, Pt520, etc. are all different. This is because the ligand unit containing pyridine heterocycle has a large structural change. The LUMO energy level of Pt518 is concentrated on the pyridine unit, while the LUMO energy level of Pt520 is concentrated on the azacarbazole unit. This shows that the ligand units containing different heterocycles can effectively regulate the LUMO energy level distribution and energy level, which is conducive to further regulation of the photophysical properties of the complex. The above experimental data and theoretical calculation results fully demonstrate that the tetradentate metal platinum complex phosphorescent material based on pyridine heterocycles, benzoazoles and carbazole derivatives developed in the present invention application has the characteristics of easy adjustment of HOMO and LUMO orbital energy levels and high phosphorescence quantum efficiency, indicating that it has great application prospects in the field of OLED.

[0153] Fabrication of OLED devices:

[0154] In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer, and the hole transport material can be preferably selected from known or unknown materials. The present invention can select one or more of the following hole transport material structures, but it does not mean that the present invention is limited to the following structures:

[0155]

[0156]

[0157]

[0158]

[0159]

[0160] In a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention comprises one or more p-type dopants. The present invention may select one or more of the following p-type dopant structures, but it does not mean that the present invention is limited to the following structures:

[0161]

[0162]

[0163] In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of compounds ET-1 to ET-77, but this does not mean that the present invention is limited to the following structure:

[0164]

[0165]

[0166]

[0167] The electron transport layer may be formed of an organic material and one or more n-type dopants (such as LiQ, LiTHPh, etc.).

[0168]

[0169]

[0170] As a reference preparation method for an OLED device embodiment, a p-doped material is evaporated on the surface of an ITO glass or an anode with a light-emitting area of ​​2mm×2mm, or the p-doped material is co-evaporated with a hole injection material at a concentration of 1% to 50% to form a 5-100nm hole injection layer (HIL), a 5-200nm hole transport layer (HTL), and then a 10-100nm light-emitting layer (EML) (which may contain the compound described in the present invention) is formed on the hole transport layer, and an electron transport layer (ETL) of 20-200nm and a cathode of 50-200nm are formed; if necessary, an electron blocking layer (EBL) is added between the HTL and EML layers, and an electron injection layer (EIL) is added between the ETL and the cathode to manufacture an OLED device. The OLED is tested by a standard method. The device materials involved in the present invention can be obtained by known synthesis methods unless otherwise specified.

[0171] In a preferred specific embodiment, the structure of device example 1 provided by the present invention is: ITO / P-4 (10nm) / NPD (60nm) / HT-85 (5nm) / Pt1:H-2 (25nm) (Pt1:H-2 mass ratio is 10:90) / ET-8 (5nm) / ET-14 or BPyTP (40nm) / LiQ (1nm) / Al (100nm).

[0172] Device Examples 2 to 33 and Comparative Example 1 were prepared using structures similar to that of Device Example 1, except that Pt2, Pt3, Pt4, Pt16, Pt21, Pt62, Pt74, Pt103, Pt118, Pt128, Pt140, Pt157, Pt171, Pt190, Pt224, Pt263, Pt276, Pt319, Pt345, Pt395, Pt410, Pt442, Pt486, Pt508, Pt513, Pt514, Pt515, Pt516, Pt517, Pt518, Pt519, Pt520 and R1 were used to replace Pt1 in Device Example 1. The luminescence characteristics of the comparative examples and device examples prepared above were tested by standard methods, and the data are shown in Table 2. The device structures involved are as follows:

[0173]

[0174] Table 2 Device performance of some phosphorescent materials

[0175]

[0176]

[0177]

[0178] It can be seen from Table 2 that compared with Comparative Example 1, device examples 1 to 33 prepared in the present application all have lower turn-on voltages and higher external quantum efficiencies, indicating that the tetradentate metal platinum complex phosphorescent material provided by the present invention has certain commercial application value.

[0179] It will be appreciated by those skilled in the art that the above embodiments are specific embodiments for implementing the present invention, and in practical applications, various changes may be made to them in form and detail without departing from the spirit and scope of the present invention. For example, many of the substituent structures described herein may be replaced with other structures without departing from the spirit of the present invention.

Claims

1. A tetradentate metal platinum complex phosphorescent material, characterized in that: It has the general structure shown in formula (I-2): In formula (I-2), Y 6 Independently selected from C or N; Y 1 -Y 5 , Y 7 -Y 28 Selected from C; X1 is selected from NR4; the R4 is independently selected from hydrogen, halogen, C1-C30 alkyl, substituted or unsubstituted C6-C60 aryl, C1-C30 heterocycloalkyl, and when containing substituents, the substituents are selected from one or more of deuterium, halogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, and phenyl; R a , R b , R c , R d , R e , R g and R h Each independently represents a single substitution to the maximum amount of substitution, or no substitution; R a -R e Each is independently selected from hydrogen, halogen, substituted or unsubstituted C1-C30 alkyl, C6-C60 aryl; when containing a substituent, the substituent is selected from deuterium and halogen; R g and R h Each is independently selected from hydrogen, and C1-C30 alkyl.

2. The tetradentate metal platinum complex phosphorescent material according to claim 1, characterized in that: The R a , R b , R c , R d and R e Each is independently selected from hydrogen, deuterium, F, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, phenyl, furanyl, benzofuranyl, pyridyl, and the group consisting of.

3. The tetradentate metal platinum complex phosphorescent material according to claim 1, characterized in that: The R g and R h Each is independently selected from hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and 2-methylbutyl.

4. A tetradentate metal platinum complex phosphorescent material, characterized in that: The tetradentate metal platinum complex phosphorescent material is selected from any one of the following structural formulas.

5. Use of the tetradentate metal platinum complex phosphorescent material according to any one of claims 1 or 4 in electronic devices, wherein the electronic devices are selected from one or more of organic electroluminescent devices, organic integrated circuits, organic field effect transistors, organic thin film transistors, organic light emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field quenching devices, light emitting electrochemical cells or organic laser diodes.

6. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a cathode, an anode and an organic functional layer therebetween; the organic functional layer comprises the tetradentate metal platinum complex phosphorescent material as claimed in any one of claims 1 or 4.

7. The organic electroluminescent device according to claim 6, characterized in that: The organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises the tetradentate metal platinum complex phosphorescent material according to any one of claims 1 or 4.

8. The organic electroluminescent device according to claim 7, characterized in that: The luminescent layer also contains a main body material, and the mass percentage of the tetradentate ring metal platinum complex phosphorescent material is between 1% and 50%.

9. An organic optoelectronic device, characterized in that: The organic photoelectric device comprises: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; and a second electrode, which is on the organic light-emitting functional layer; wherein the organic light-emitting functional layer contains the tetradentate metal platinum complex phosphorescent material according to any one of claims 1 or 4.

10. A composition, characterized in that The composition comprises the tetradentate metal platinum complex phosphorescent material according to any one of claims 1 or 4.

11. A preparation, characterized in that The preparation comprises the tetradentate metal platinum complex phosphorescent material according to any one of claims 1 or 4 and at least one solvent.

12. A display device, characterized in that: The device comprises one or more of the organic electroluminescent devices according to any one of claims 6 to 8.

13. A lighting device, characterized in that: The device comprises one or more of the organic electroluminescent devices according to any one of claims 6 to 8.

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